"Fearless" is not a compliment

Have you ever worried you do not have what it takes to live your best life? Maybe you want to invest in the stock market, but you are afraid the stocks you pick will tank1. Or you want to buy a rental property but are afraid your numbers are wrong or that you will pick the wrong tenants2.

This is nothing to be ashamed of. Your concerns are valid. Listen to them. Anyone who tells you to do otherwise is not your friend.

I have worked with people others have admiringly called "fearless." Every single one was a disaster. I would rather bring a knife to a gunfight than a partner too stupid to be afraid. Ask me about it some day, and I will show you the scars they earned me.

Fear helped keep my identity as an FBI agent a secret when I worked undercover. After changing careers and becoming an attorney, fear helped drag me back from the brink of a fate quite literally worse than death when I realized the law firm I worked at was unethical3 . I used to run an illegal underground fighting ring4, so trust me when I say any contender who does not feel fear is a contender who is not going to last long.

Fear is an essential survival skill. Do not tune it out. Instead, turn it up. Listen to what it has to tell you.

If you are worried that a particular stock is going to tank, consider reducing your position. Re-check the fundamentals. What is their growth curve? Is there new competition? Who is in charge? How will the company perform if there is a recession? A depression? A war? Can you diversify your portfolio to reduce risk? Let your fear drive your research, and eventually you will know the path forward that works for you.

If you are worried about a property as a rental investment, hedge your bets. Increase your margin by offering less and be prepared to walk away if they do not bite5. Pay for another, more thorough inspection. Bump up your projected vacancy rates and see if the numbers still work. Read up on how to screen tenants. Check your network and see if there is a good renter ready to go. Most importantly, do not put money into a mortgage you can't afford to cover or walk away from.

Fear is not a symptom of fecklessness. Fear is not the root cause of inaction, or the reason parts of your life feel unsatisfying. Fear is your hidden brain's way of telling yourself that it is time to put in more work.